CN103620009A - Biphenol ether compounds as markers for liquid hydrocarbons and other fuels and oils - Google Patents

Biphenol ether compounds as markers for liquid hydrocarbons and other fuels and oils Download PDF

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Publication number
CN103620009A
CN103620009A CN201280028970.1A CN201280028970A CN103620009A CN 103620009 A CN103620009 A CN 103620009A CN 201280028970 A CN201280028970 A CN 201280028970A CN 103620009 A CN103620009 A CN 103620009A
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fuel
petroleum hydrocarbon
alkyl
compound
general formula
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CN103620009B (en
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G·D·格林
R·斯韦多
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Dow Global Technologies LLC
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Angus Chemical Co
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    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10L—FUELS NOT OTHERWISE PROVIDED FOR; NATURAL GAS; SYNTHETIC NATURAL GAS OBTAINED BY PROCESSES NOT COVERED BY SUBCLASSES C10G, C10K; LIQUEFIED PETROLEUM GAS; ADDING MATERIALS TO FUELS OR FIRES TO REDUCE SMOKE OR UNDESIRABLE DEPOSITS OR TO FACILITATE SOOT REMOVAL; FIRELIGHTERS
    • C10L1/00—Liquid carbonaceous fuels
    • C10L1/003—Marking, e.g. coloration by addition of pigments
    • G—PHYSICS
    • G01—MEASURING; TESTING
    • G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
    • G01N33/00—Investigating or analysing materials by specific methods not covered by groups G01N1/00 - G01N31/00
    • G01N33/22—Fuels, explosives
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10L—FUELS NOT OTHERWISE PROVIDED FOR; NATURAL GAS; SYNTHETIC NATURAL GAS OBTAINED BY PROCESSES NOT COVERED BY SUBCLASSES C10G, C10K; LIQUEFIED PETROLEUM GAS; ADDING MATERIALS TO FUELS OR FIRES TO REDUCE SMOKE OR UNDESIRABLE DEPOSITS OR TO FACILITATE SOOT REMOVAL; FIRELIGHTERS
    • C10L1/00—Liquid carbonaceous fuels
    • C10L1/10—Liquid carbonaceous fuels containing additives
    • C10L1/14—Organic compounds
    • C10L1/18—Organic compounds containing oxygen
    • C10L1/185—Ethers; Acetals; Ketals; Aldehydes; Ketones
    • C10L1/1852—Ethers; Acetals; Ketals; Orthoesters
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M171/00—Lubricating compositions characterised by purely physical criteria, e.g. containing as base-material, thickener or additive, ingredients which are characterised exclusively by their numerically specified physical properties, i.e. containing ingredients which are physically well-defined but for which the chemical nature is either unspecified or only very vaguely indicated
    • C10M171/007—Coloured or dyes-containing lubricant compositions
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10L—FUELS NOT OTHERWISE PROVIDED FOR; NATURAL GAS; SYNTHETIC NATURAL GAS OBTAINED BY PROCESSES NOT COVERED BY SUBCLASSES C10G, C10K; LIQUEFIED PETROLEUM GAS; ADDING MATERIALS TO FUELS OR FIRES TO REDUCE SMOKE OR UNDESIRABLE DEPOSITS OR TO FACILITATE SOOT REMOVAL; FIRELIGHTERS
    • C10L2200/00—Components of fuel compositions
    • C10L2200/04—Organic compounds
    • C10L2200/0407—Specifically defined hydrocarbon fractions as obtained from, e.g. a distillation column
    • C10L2200/0415—Light distillates, e.g. LPG, naphtha
    • C10L2200/0423—Gasoline
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10L—FUELS NOT OTHERWISE PROVIDED FOR; NATURAL GAS; SYNTHETIC NATURAL GAS OBTAINED BY PROCESSES NOT COVERED BY SUBCLASSES C10G, C10K; LIQUEFIED PETROLEUM GAS; ADDING MATERIALS TO FUELS OR FIRES TO REDUCE SMOKE OR UNDESIRABLE DEPOSITS OR TO FACILITATE SOOT REMOVAL; FIRELIGHTERS
    • C10L2200/00—Components of fuel compositions
    • C10L2200/04—Organic compounds
    • C10L2200/0461—Fractions defined by their origin
    • C10L2200/0469—Renewables or materials of biological origin
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10L—FUELS NOT OTHERWISE PROVIDED FOR; NATURAL GAS; SYNTHETIC NATURAL GAS OBTAINED BY PROCESSES NOT COVERED BY SUBCLASSES C10G, C10K; LIQUEFIED PETROLEUM GAS; ADDING MATERIALS TO FUELS OR FIRES TO REDUCE SMOKE OR UNDESIRABLE DEPOSITS OR TO FACILITATE SOOT REMOVAL; FIRELIGHTERS
    • C10L2200/00—Components of fuel compositions
    • C10L2200/04—Organic compounds
    • C10L2200/0461—Fractions defined by their origin
    • C10L2200/0469—Renewables or materials of biological origin
    • C10L2200/0476—Biodiesel, i.e. defined lower alkyl esters of fatty acids first generation biodiesel
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10L—FUELS NOT OTHERWISE PROVIDED FOR; NATURAL GAS; SYNTHETIC NATURAL GAS OBTAINED BY PROCESSES NOT COVERED BY SUBCLASSES C10G, C10K; LIQUEFIED PETROLEUM GAS; ADDING MATERIALS TO FUELS OR FIRES TO REDUCE SMOKE OR UNDESIRABLE DEPOSITS OR TO FACILITATE SOOT REMOVAL; FIRELIGHTERS
    • C10L2230/00—Function and purpose of a components of a fuel or the composition as a whole
    • C10L2230/16—Tracers which serve to track or identify the fuel component or fuel composition
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/04—Ethers; Acetals; Ortho-esters; Ortho-carbonates
    • G—PHYSICS
    • G01—MEASURING; TESTING
    • G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
    • G01N33/00—Investigating or analysing materials by specific methods not covered by groups G01N1/00 - G01N31/00
    • G01N33/26—Oils; viscous liquids; paints; inks
    • G01N33/28—Oils, i.e. hydrocarbon liquids
    • G01N33/2835—Oils, i.e. hydrocarbon liquids specific substances contained in the oil or fuel
    • G01N33/2882—Markers
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
    • Y10T436/00—Chemistry: analytical and immunological testing
    • Y10T436/20—Oxygen containing

Abstract

A method for marking a petroleum hydrocarbon or a liquid biologically derived fuel by adding to the petroleum hydrocarbon or liquid biologically derived fuel at least one compound having formula (I), wherein R represents C1-C18 alkyl, C3-C18 alkenyl or C3-C18 alkynyl.

Description

Bis-phenol ether compound for liquid hydrocarbon and other fuel and the oily thing that serves as a mark
The present invention relates to a kind of suitable compound marking liquid hydrocarbons and other fuel and oily method used.
With various chemical markers, to petroleum hydrocarbon and other fuel, be well-known in the art with the way that oil carries out mark.People are used for this purposes by various compounds, also by a lot of technology, carry out certification mark thing, for example, adopt absorption spectrum and mass-spectrometric technique.For example, United States Patent (USP) the 7th, has disclosed for 858, No. 373 various organic compound for liquid hydrocarbon and other fuel and oil are carried out to mark.But people need other the tagged compound for these products always.Can, in the situation that the ratio of amount forms the coding that is labeled product, the combination of marker be used as to numerical markings system.People wish other the compound that can be used as fuel and lubricant marker, to obtain available code as much as possible.Problem to be solved by this invention is to find other can being used for to liquid hydrocarbon and other fuel and the oily marker that carries out mark.
Summary of the invention
The invention provides a kind of method that fuel to petroleum hydrocarbon or liquid bio source carries out mark; Described method comprises in the fuel in described petroleum hydrocarbon or liquid bio source and adds the compound shown at least one general formula (I)
Figure BDA0000436149970000011
Wherein, R represents C 1-C 18alkyl, C 3-C 18thiazolinyl or C 3-C 18alkynyl.
Detailed Description Of The Invention
Unless otherwise indicated, otherwise percentage ratio is weight percentage (% by weight), and the unit of temperature is ℃.The unit of concentration is in w/w or in every 1,000,000/umber (" ppm ") of weight/volume (mg/litre); Preferably in weight/volume.Term " petroleum hydrocarbon " represents mainly have the product that hydrocarbon forms, but they also can comprise a small amount of oxygen, nitrogen, sulphur or phosphorus; The product that petroleum hydrocarbon comprises crude oil and is derived from oil refining process; They comprise for example crude oil, lubricating oil, hydraulic fluid, braking fluid, gasoline, diesel oil fuel, kerosene, jet fuel and heated oil.Tagged compound of the present invention can be added into the fuel in petroleum hydrocarbon or liquid bio source; The latter's example is biodiesel fuel, ethanol, butanols, Ethyl Tertisry Butyl Ether or its mixture.If a kind of material is liquid in the time of 20 ℃, think that this material is liquid.Biodiesel fuel is the fuel of biogenetic derivation, comprises fatty acid alkyl ester, particularly the mixture of fatty acid methyl ester.Conventionally by vegetables oil new or recirculation is carried out to transesterify, make biodiesel fuel, but also can use animal tallow.Alcohol fuel is any fuel that comprises ethanol, can be pure alcohol form, or can comprise the mixture of ethanol and petroleum hydrocarbon, for example " ethanol-gasoline "." alkyl " is replacement or the unsubstituted alkyl that comprises 1-18 carbon atom, and it can have straight chain, branching or ring texture, or its combination." thiazolinyl " or " alkynyl " is respectively the alkyl that comprises one or more pair of key or triple bond.Can on alkyl, replace with one or more hydroxyls or alkoxyl group.Preferably, alkyl is unsubstituted.Preferably, alkyl is acyclic.Preferably the various elements that, compound of the present invention comprises exist according to its natural isotopic ratio.
Preferably, R represents C 1-C 18alkyl or C 3-C 18thiazolinyl, preferably C 2-C 18alkyl or C 3-C 18thiazolinyl, preferably C 1-C 18alkyl, preferably C 3-C 16alkyl or C 3-C 16thiazolinyl, preferably C 2-C 18alkyl, preferably C 4-C 16alkyl or C 4-C 16thiazolinyl, preferably C 4-C 16alkyl, preferably C 5-C 16alkyl, preferably C 8-C 14alkyl.In general formula (I), the optional position that described-OR group can be on phenyl ring, preferably the position on each ring identical (for example 2,2 '-or 4,4 '-replace), preferably, described-OR group on phenyl ring 2,2 '-position, the compound of general formula (I) has following structure:
In the method for the invention, the minimum of preferred every kind of marker is at least 0.01ppm, is preferably at least 0.02ppm, is preferably at least 0.05ppm, is preferably at least 0.1ppm, is preferably at least 0.2ppm.Preferably, the maximum of various markers is 50ppm, preferably 20ppm, preferably 15ppm, preferably 10ppm, preferably 5ppm, preferably 2ppm, preferably 1ppm, preferably 0.5ppm.Preferably, the maximum total amount of tagged compound is 100ppm, preferably 70ppm, preferably 50ppm, preferably 30ppm, preferred 20ppm, preferably 15ppm, preferably 12ppm, preferably 10ppm, preferably 8ppm, preferred 6ppm, preferably 4ppm, preferably 3ppm, preferably 2ppm, preferably 1ppm.Preferably, in the fuel in the petroleum hydrocarbon being labeled or liquid bio source, tagged compound cannot arrive by visual detection, that is to say, whether the fuel that can not measure petroleum hydrocarbon or liquid bio source by visual inspection color or further feature comprises tagged compound.Preferably, tagged compound is not naturally occurring compound in the fuel in its petroleum hydrocarbon adding or liquid bio source, not as the component of the fuel in petroleum hydrocarbon or liquid bio source itself, or as use therein additive yet.
Preferably, the log P value of described tagged compound is at least 3, and wherein P is 1-Octanol/water Partition Coefficients.Preferably, the log P of described tagged compound is at least 4, is preferably at least 5.By the Log P value of test determination report, can not use Meylan in the literature, W.M & Howard, P.H., IPharm.Sci., the 84th volume, the method estimation that 83-92 page (1995) discloses.Preferably, the fuel in described petroleum hydrocarbon or liquid bio source is petroleum hydrocarbon, biodiesel fuel or alcohol fuel; Preferably petroleum hydrocarbon or biodiesel fuel; Petroleum hydrocarbon preferably; Preferably crude oil, gasoline, diesel oil fuel, kerosene, jet fuel or heated oil; Gasoline preferably.
Be preferably, certification mark compound in the following manner, use chromatographic technique that tagged compound is separated from the component of the fuel in described petroleum hydrocarbon or liquid bio source at least in part, described chromatographic technique comprises for example gas-chromatography, liquid chromatography, thin-layer chromatography, paper chromatography, adsorption chromatography, affinity chromatogram, capillary electrophoresis, ion-exchange and molecular-exclusion chromatography.After carrying out chromatographic run, carry out at least one in following operation: (i) mass spectroscopy, and (ii) FTIR.The discriminating of tagged compound is preferably determined by mass spectroscopy.Preferably, do not carrying out under the condition of any separation the tagged compound in the fuel in use mass spectroscopy detection petroleum hydrocarbon or liquid bio source.Or, can tagged compound be concentrated by for example distilling the stronger component of some volatility of the fuel in petroleum hydrocarbon or liquid bio source, then analyze.
Preferably, exist and surpass a kind of tagged compound.Use multiple tagged compound to be convenient to them to sneak in the petroleum hydrocarbon of information of coding or the fuel in liquid bio source, the information of this coding can be used for differentiating the source of fuel in described petroleum hydrocarbon or liquid bio source and other feature.Described coding comprises kind and the relative quantity of tagged compound, for example fixed integer ratio.Can use a kind of, two kinds, three kinds or more kinds of tagged compound to form described coding.Can be by the marker of tagged compound of the present invention and other kinds (for example, by the marker of absorption spectrometry) combination, the marker of described other kinds comprises with those described in Publication about Document: United States Patent (USP) the 6th, 811, No. 575; No. 79,749, No. 2004/0250469th, U.S. Patent Application Publication and European Application Publication Isosorbide-5-Nitrae.Tagged compound is introduced directly in the fuel in petroleum hydrocarbon or liquid bio source, or add in the additive packing that comprises other compound, for example, for the antiwear additive of lubricant, be used for the washing composition of gasoline etc., described additive packing added in the fuel in petroleum hydrocarbon or liquid bio source.
Compound of the present invention can be prepared by methods known in the art.For example, existing under the condition of alkali, according to following equation, alkyl halide can react with bis-phenol
Figure BDA0000436149970000041
Embodiment
Synthesizing as described in the following Examples of bis-phenol ether:
2,2 '-bis-(dodecyloxy)-1,1 '-biphenyl:100 milliliters of three-necked flasks have assembled magnetic stirring apparatus, with the reflux exchanger of nitrogen protection and with the heating mantles of temperature regulator and thermopair.By 3.74 grams of (0.02 moles) 2,2 '-bis-phenol, 2.8 grams of (0.04 mole, 85 % by weight) potassium hydroxide and 25 milliliters of methyl-sulphoxides add in flask.Under nitrogen, mixture is stirred and is heated to 100 ℃ simultaneously.Approximately 2 1/ 2after hour, potassium hydroxide dissolves, and mixture is cooled to approximately 70 ℃.Disposable (9.60 milliliters of the lauryl bromides that add; D1.038; 9.97 gram; 0.04 mole).Observe heat release to approximately 86 ℃.After heat release is gone down, at 70 ℃, reaction mixture is stirred.After approximately 5 hours, reaction mixture is poured in approximately 400 ml waters.By filtration, collect separated white solid, with several parts of moisture, on strainer, it is washed several times.First this solid is carried out to dry air, then in the vacuum drying oven at 50 ℃, be dried approximately 2 hours.The output of product is 9.49 grams (91%), and fusing point is 33-35 ℃.With IR, 1h-NMR, 13c-NMR and GC/MS analyze to confirm structure.
When reaction mixture in water quencher after product with oily matter isolated in form situation out in, with ether extracts to replace filtration.
2 of preparation, 2 '-bis-phenol ether:
R Productive rate % MP,℃
? ? ?
n-C 8H 17(BOct-BBPh) 94 (oily matter)
n-C 10H 21(BDec-BBPh) 97 (oily matter)
n-C 12H 25(BDD-BBPh) 91 33–35
n-C 14H 29(BTD-BBPh) 94 33-35
the GC performance of bis-phenol ether
Use FID (flame ionization detector) to complete detection.
The comparison of GC parameter:
Figure BDA0000436149970000051
Figure BDA0000436149970000052

Claims (9)

1. the fuel to petroleum hydrocarbon or liquid bio source carries out the method for mark; Described method comprises in the fuel in described petroleum hydrocarbon or liquid bio source and adds the compound shown at least one general formula (I)
Figure FDA0000436149960000011
Wherein, R represents C 1-C 18alkyl, C 3-C 18thiazolinyl or C 3-C 18alkynyl.
2. the method for claim 1, is characterized in that, the content of the various compounds of general formula (I) is 0.01-20ppm.
3. method as claimed in claim 2, is characterized in that ,-OR group on the phenyl ring of general formula (I) 2, on 2 '-position.
4. method as claimed in claim 3, is characterized in that, R represents C 2-C 18alkyl or C 3-C 18thiazolinyl.
5. method as claimed in claim 4, is characterized in that, the content of the various compounds of general formula (I) is 0.01-10ppm.
6. method as claimed in claim 5, is characterized in that, R represents C 3-C 16alkyl or C 3-C 16thiazolinyl.
7. method as claimed in claim 6, is characterized in that, described method also comprises the compound that detects general formula (I) by mass spectroscopy.
8. method as claimed in claim 7, is characterized in that, R represents C 4-C 16alkyl.
9. method as claimed in claim 8, is characterized in that, the fuel in described petroleum hydrocarbon or liquid bio source is petroleum hydrocarbon, biodiesel fuel or alcohol fuel.
CN201280028970.1A 2011-06-30 2012-06-28 Biphenol ether compounds as markers for liquid hydrocarbons and other fuels and oils Active CN103620009B (en)

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US201161502974P 2011-06-30 2011-06-30
US61/502,974 2011-06-30
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US20140134746A1 (en) 2014-05-15
ES2694823T3 (en) 2018-12-27
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